Chem 363, Section 2
Exam 3, May 28, 2008
Name: Answer Key Student ID#:_________
1) (4 pts.) Give the correct IUPAC name for the following compound.
Answer:
3-Ethyl-2-methyl-cyclopentanamine
2) (8 pts.) Draw structures which correspond to the following IUPAC names.
a. 2-Ethyl-butylamine b. N-Ethyl-N-propyl-hexylamine
Answer:
a. b.
3) (20 pts.) Give short answers to the following questions.
a. Classify each of the following nitrogen atoms in the following compounds as primary, secondary, tertiary, or quaternary.
Ephedrine Amphetamine Mepiquat chloride
______ ______ ______
Answer:
secondary primary quaternary
b. Give a specific example for a Friedel-Crafts alkylation reaction. Explain what is the role of the catalyst.
Answer:
The AlCl3 is a Lewis acid catalyst that assists in the ionization of the alkyl halide to give the carbocation electrophile.
c. Give a specific example for a nucleophilic aromatic substitution reaction.
Answer:
d. Rank the following compounds in order of increasing basicity. Label the least basic compound “1” and the most basic compound “4.” Place the number corresponding to the compound’s rank in the blank below the compound.
______ ______ ______ ______
Answer:
__3__ __2__ __4__ __1__
e. Rank the compounds below according to their reactivity toward electrophilic aromatic substitution (most reactive = 1, least reactive = 3). Place the number corresponding to the compound’s relative reactivity in the blank below the compound.
____ ____ ____
Answer:
__3__ __1__ __2__
4) (48 pts.) Complete the following reactions.
a.
Answer:
b.
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c.
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d.
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e.
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f.
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g.
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h.
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i.
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j.
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k.
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l.
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5) (10 pts.) Write the complete stepwise mechanism for the formation of the ortho product in the following reaction. Show all intermediate structures and the electron flow using the curved arrow convention. Draw resonance structures for the intermediate carbocation.
Answer:
6) (10 points) Using benzene (C6H6) synthesize the following compound. More than one step will be required. Show all reagents and all intermediate compounds.
Answer:
Bonus Question
7) (5 bonus pts.) List the five major types of electrophilic aromatic substitution reactions.
Answer:
Halogenation, nitration, sulfonation, alkylation, and acylation